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5 takeaways from Questlove’s new book on creativity

4 min read

In Creative Quest, the drummer, DJ, and Late Night musical director dives into his own successes and failures, and shares inspiration from a few of his A-list friends.

There is certainly no shortage of books about creativity. In recent years, writers Austin Kleon and Elizabeth Gilbert have published best-sellers on the subject, joining earlier offerings from choreographer Twyla Tharp and IDEO co-founders Tom and David Kelley. In fact, in the very first pages of his new book Creative Quest, Questlove (aka Ahmir Khalib Thompson) reveals his own skepticism toward the genre. So rather than offer up a how-to manual or argue for creativity as therapy, the Roots drummer, DJ, and Late Night star simply shares his own successes and failures, along with those of friends and collaborators from Ava DuVernay, Bjork, and Neil deGrasse Tyson to David Lynch, Prince, and Usher.

At times, the writing can feel a bit train-of-thought, like a good friend opening a laptop to share a collection of favorite songs, bookmarks, or YouTube videos—some you’ve no doubt seen before, and some of which are complete revelations. In the end, the book feels less like a set of hard-and-fast principles and more like a late-night pep talk from someone who’s been there before. Read on for a few of our favorite takeaways.

Seek out boredom—and embrace it

When Quest was writing his memoir Mo Meta Blues, he found himself hopelessly distracted by the internet, which made procrastination far too tempting.

“With just a single mouse click I could listen to an Outkast demo or read about zoning in Philadelphia, or hop back in time and find a vintage interview with Wilson Pickett,” he writes. “When I find myself going to more than one website in rapid succession… I stop. I shut the computer or at least close my eyes for a second… and I let the distraction become boredom. And when the distraction shifts into boredom, that’s the seed of something creative. On the face of it, it doesn’t make any sense. Boredom seems like the least creative feeling. But it’s actually a way of clearing space for a new idea to spring back up.

“When the distraction shifts into boredom, that’s the seed of something creative.”

“Let yourself go to the sense of being disconnected and meaningless. Let it wash over you a little bit before you come up gasping for air. Creativity is a fight against that insignificance. You have to remember that you’re insignificant, but also that you are potentially more significant than all the noise that’s being supplied to you at any moment.”

Start with the end in mind

Earlier in his career, before starting work on a Roots album, Quest would imagine the eventual Rolling Stone cover and the five-star review he hope to receive. He’d even lay out the review on a sheet of paper and sketch an illustration to go along with it.

“If you’re a writer, imagine the blurbs that will be on the paperback,” he says. “If you’re a painter, imagine what people will say when they’re standing in front of your canvas. When you’re on the outside of your own work looking in, you’ll be able to see the overall shape of it, which will help you realize that you’re on the right track (or, alternatively, that you’re not). It’s a way of journeying to the center of what the idea will become.”

Quest points out that when Amazon generates ideas for products like Echo (aka “Alexa”), the project starts with a press release, as if the product already exists. Amazon know consumers won’t care about the nuts and bolts; they’ll care about what the product does for them. By keeping that idea at the forefront from Day 1, they ensure that the creative process stays on track.

Recognize that failure can be liberating

“There are at least two lessons to take away from stories of failure,” Quest writes. “The first, of course, is not to be afraid of it. Any career, if it is to be a long career, includes a mix of successes and failures, and it should. That mix is oxygen-rich. It keeps you breathing.”

Quest details Pitchfork’s scores for The Roots’ early albums from a 9.4 for 1999’s Things Fall Apart and an 8.1 for Phrenology to a lackluster 5.4 for The Tipping Point, his own definition of failure.

“Creative failures can feel like near-death experiences, and surviving them can create a sense of liberation.”

“Failure is not fatal. For starters, it can be a motivator. Smooth sailing isn’t always the best way to convince yourself to put your nose back to the grindstone. Struggle and frustration and fear can be great tools for learning to focus and recharge yourself. David Bowie once said that creativity is ‘one of the few human endeavors where you can crash your airplane and walk away from it.’ Creative failures can feel like near-death experiences, and surviving them can create a sense of liberation. When you walk away from your crashed airplane, you’re playing with house money. You can do anything—and hopefully you will.”

In the years that followed, Pitchfork’s editors scored The Roots’ successive albums better and better, and in 2010 the appropriately titled How I Got Over received an 8.1. And regardless of whether the numbers went up or down, they had an impact.

“It’s not about whether or not [people] like your work so much as whether or not the way they feel about it motivates you to make more work,” he says. “Creativity only fails when it stops.”

Embrace the things that scare you

Quest discusses Eminem’s early years and his ability to embrace “Yes, and…” thinking, which has been popularized by improv comedians. Like most famous figures, Quest had experienced fans that made him feel a little uneasy, including a woman who appeared on The Roots’ tour bus after three consecutive shows, which left him envisioning “Saw-type hostage situations” that left him sleepless.

“A few years later, Eminem came out with ‘Stan’ and it all came clear to me—you weren’t supposed to banish the idea. You were supposed to embrace it,” he says. “In the privacy of your own home, in the comfort of your own head, you’re supposed to play it out to its natural conclusion. Eminem didn’t put a should-I-really-say-that cap on his idea. He didn’t put a socially acceptable filter on it. Many artists would have turned away from that initial idea… but a few have allowed themselves the chance to write a great song.”

Photo by Michael Baca

Be a little bit weird

While conducting research for the book, Quest came across the article Why Weird People Are Often More Creative. In it, the writer cites a 2003 study from Harvard psychologist Shelley Carson which suggests that when you lower your cognitive inhibitions, “more information enters into your conscious mind, which you can then tinker with and recombine. The result: creative ideas.”

Or as Quest says, “If we’re always discarding our thoughts to fit in with what’s acceptable or correct or accurate, we’re not going to have ideas that leap away from the ideas that are already out there.” Like, say, an app that invites complete strangers to stay in your home or a hip-hop Broadway musical about one of our nation’s Founding Fathers.

Quest also cites a study that tested college students on puzzles that involved word-play or novel solutions. Oddly enough, students’ creative problem solving improved by about 20 percent when they were tired and therefore, less able to apply logical thinking. “To truly get in touch with your creative side and the ideas it generates, you have to look through the organized and focused thoughts and find out what’s behind them,” he writes. “There might be nothing back there, or there might be something brilliant.”

Scott Kirkwood is a freelance copywriter and creative director in Denver, CO, with a focus on do-gooders, graphic design, and the great outdoors. His editorial work has appeared in 99U, Communication Arts, HOW, and Modern in Denver.